(4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: (4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 766514-65-2
• Molecular Formula: C₄₇H₆₅NO₁₀SSi₂
• Molecular Weight: 892.271
• Mol file: 766514-65-2.mol

Synonyms:(4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of (4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

There total 5 articles about (4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

(4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (766514-64-1) + biphenyl-4-yl-acetyl chloride (39889-69-5) → (4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (766514-65-2)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo049441h

Reference yield:

2-tert-butoxycarbonylamino-4-oxo-hexanedioic acid 1-benzyl ester 6-(2-trimethylsilanyl-ethyl) ester (766514-48-1) → (4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (766514-65-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / pyridine; phthalimidesulfenyl chloride / CHCl₃ / 40 h / 50 - 55 °C

2: TMSCl / CH₂Cl₂ / 1.5 h / 20 °C

3: 50 percent / NEt₃ / CH₂Cl₂ / 1 h / 20 °C

With pyridine; chloro-trimethyl-silane; phthalimidesulfenyl chloride; triethylamine; In dichloromethane; chloroform;

DOI:10.1021/jo049441h

Reference yield:

(4aR,6R,7R,8S,8aR)-3-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-7-hydroxy-8-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (766514-63-0) → (4aR,6R,7R,8S,8aR)-3-[(S)-2-Benzyloxycarbonyl-2-(2-biphenyl-4-yl-acetylamino)-ethyl]-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester (766514-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: TMSCl / CH₂Cl₂ / 1.5 h / 20 °C

2: 50 percent / NEt₃ / CH₂Cl₂ / 1 h / 20 °C

With chloro-trimethyl-silane; triethylamine; In dichloromethane;

DOI:10.1021/jo049441h

upstream raw materials:

(4aR,6R,7R,8S,8aR)-3-((S)-2-Amino-2-benzyloxycarbonyl-ethyl)-7-hydroxy-6-hydroxymethyl-8-triisopropylsilanyloxy-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester

biphenyl-4-yl-acetyl chloride

2-tert-butoxycarbonylamino-4-oxo-hexanedioic acid 1-benzyl ester 6-(2-trimethylsilanyl-ethyl) ester

(4aR,6R,7R,8S,8aR)-3-((S)-2-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-ethyl)-7-hydroxy-8-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene-2-carboxylic acid 2-trimethylsilanyl-ethyl ester